(E)-1-(4-Aminophenyl)-3-(pyridin-3-yl)prop-2-en-1-one

The title chalcone derivative, C14H12N2O, consists of 4-aminophenyl and pyridine rings bridged by a prop-2-en-1-one unit and exists in a trans configuration with respect to the C=C double bond. The molecule is slightly twisted with a dihedral angle of 29.38 (7)° between the benzene and pyridine rings. The prop-2-en-1-one bridge is nearly planar with an r.m.s. deviation of 0.0384 (1) Å and makes dihedral angles of 15.40 (9) and 16.30 (9)°, respectively, with the benzene and pyridine rings. In the crystal, molecules are linked by N—H⋯N and N—H⋯O hydrogen bonds into a layer parallel to the ab plane. A π–π interaction with a centroid–centroid distance of 3.6946 (10) Å is also observed.

The title chalcone derivative, C 14 H 12 N 2 O, consists of 4aminophenyl and pyridine rings bridged by a prop-2-en-1one unit and exists in a trans configuration with respect to the C C double bond. The molecule is slightly twisted with a dihedral angle of 29.38 (7) between the benzene and pyridine rings. The prop-2-en-1-one bridge is nearly planar with an r.m.s. deviation of 0.0384 (1) Å and makes dihedral angles of 15.40 (9) and 16.30 (9) , respectively, with the benzene and pyridine rings. In the crystal, molecules are linked by N-HÁ Á ÁN and N-HÁ Á ÁO hydrogen bonds into a layer parallel to the ab plane. Ainteraction with a centroid-centroid distance of 3.6946 (10) Å is also observed.

Related literature
For bond-length data, see: Allen et al. (1987). For a related structure, see: Horkaew et al. (2010). For background to and applications of chalcones, see: Gaber et al. (2008); Á vila et al.  (2005). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 Table 1 Hydrogen-bond geometry (Å , ).
Moreover, chalcones have also been studied for non-linear optical (NLO) (Patil et al., 2007) and fluorescent materials (Gaber et al., 2008). These compounds have also been used for sensor, liquid crystal display and fluorescence probe for sensing of DNA or proteins (Svetlichny et al., 2007;Xu et al., 2005). These interesting properties has lead us to synthesize the title compound (I), which contains the amino and pyridine groups in order to study its bioactivity and fluorescent properties. Our results show that (I) was inactive for antibacterial and tyrosinase inhibitory activities. However (I) exhibits weak fluorescence with the maximum emission at 437 nm when was excited at 310 nm. Herein the crystal structure of (I) is reported.

Experimental
The title compound was synthesized by condensation of 4-aminoacetophenone (0.40 g, 3 mmol) with 3-pyridinecarboxaldehyde (0.18 ml, 3 mmol) in ethanol (15 ml) in the presence of 10% NaOH (aq) (5 ml). After stirring for 2 hr at room temperature, the resulting yellow solid was collected by filtration, washed with distilled diethyl ether, dried and purified by repeated recrysallization from acetone. Yellow block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from methanol by the slow evaporation of the solvent at room temperature after several days, Mp. 453-454 K.

Refinement
All H atoms were located in a difference Fourier map and refined isotropically. The highest residual electron density peak is located at 0.74 Å from C8 and the deepest hole is located at 1.35 Å from C14. Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.

Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.